Microsoft Remote Connectivity Analyzer (MRCA) test fails to Autodiscover

I'm trying to migrate mailboxes from Exchange 2007 to Office365.  Going thru the online guide to do a "cutover" migration was going ok until the point where you have to test "Autodiscover".   If I run the MRCA, it fails when selecting "Autodiscover".  If I select to "Manually Select server settings" the test will pass with a warning about the certificate.  

Outlook Web Access works ok with all users and no certificate errors in the browser.   After doing some research online for this problem, I added a CNAME for autodiscover to our DNS record and also tried opening port 80 on our firewall temporarily also, but this didn't solve issue.  I inherited this Exchange server and am not an expert on it by no means.   Attached are results from the MRCA test.
Who is Participating?

[Product update] Infrastructure Analysis Tool is now available with Business Accounts.Learn More

I wear a lot of hats...

"The solutions and answers provided on Experts Exchange have been extremely helpful to me over the last few years. I wear a lot of hats - Developer, Database Administrator, Help Desk, etc., so I know a lot of things but not a lot about one thing. Experts Exchange gives me answers from people who do know a lot about one thing, in a easy to use platform." -Todd S.

Shreedhar EtteCommented:

If you were able to complete the Outlook Connectivity test with "Manually specify server settings" then you should be able to initiate mailbox migration from office 365 portal. However you need to create migration endpoint with Manual specifications.
For autodiscover to work properly, you need not just the DNS records for it but also the ports open and redirected to the right server.  Also, you should make sure your IIS root is not redirecting to

If you are redirecting from to is fine but you'll have to have this only for this directory only;  this will allow the direct pass to  Therefore, make sure there is no redirection for the autodiscover directory either.

Now, despite the recommendations on the web about autodiscover, you can function without it!!!!.  The biggest issue will be you will have always to manually configure your email clients.  Good: users can't install their accounts on any single device they go to... Bad: they will always require you to do it for them or worst you'll have to give the info out and they will be able to installed wherever they want.

Experts Exchange Solution brought to you by

Your issues matter to us.

Facing a tech roadblock? Get the help and guidance you need from experienced professionals who care. Ask your question anytime, anywhere, with no hassle.

Start your 7-day free trial
It's more than this solution.Get answers and train to solve all your tech problems - anytime, anywhere.Try it for free Edge Out The Competitionfor your dream job with proven skills and certifications.Get started today Stand Outas the employee with proven skills.Start learning today for free Move Your Career Forwardwith certification training in the latest technologies.Start your trial today

From novice to tech pro — start learning today.